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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:41:51 UTC
Update Date2019-07-23 06:35:07 UTC
HMDB IDHMDB0041835
Secondary Accession Numbers
  • HMDB41835
Metabolite Identification
Common NameBenzidine
DescriptionBenzidine is prepared in a two step process from nitrobenzene. First, the nitrobenzene is converted to 1,2-diphenylhydrazine, usually using iron powder as the reducing agent. Treatment of this hydrazine with mineral acids induces a rearrangement reaction to 4,4'-benzidine. Smaller amounts of other isomers are also formed. The benzidine rearrangement, which proceeds intramolecularly, is a classic mechanistic puzzle in organic chemistry. Benzidine, the trivial name for 4,4'-diaminobiphenyl, is the solid organic compound with the formula (C6H4NH2)2. This aromatic amine is a component of a test for cyanide and also in the production of dyes. Benzidine has been linked to bladder and pancreatic cancer. Since August 2010 benzidine dyes are included in the EPA's List of Chemicals of Concern.
Structure
Data?1563863707
Synonyms
ValueSource
(1,1'-Biphenyl)-4,4'-diamineChEBI
4,4'-BianilineChEBI
4,4'-BiphenyldiamineChEBI
4,4'-BiphenylenediamineChEBI
4,4'-Diamino-1,1'-biphenylChEBI
4,4'-DiaminobiphenylChEBI
4,4'-DiaminodiphenylChEBI
4,4'-DiphenylenediamineChEBI
C.I. azoic diazo component 112ChEBI
p,P'-bianilineChEBI
p,P'-diaminodiphenylChEBI
p-DiaminodiphenylChEBI
4'-Amino[1,1'-biphenyl]-4-ylamine (acd/name 4.0)HMDB
4, 4'-BiphenylenediamineHMDB
Biphenyl -4,4'-ylenediamineHMDB
Fast corinth base bHMDB
p,P'-diaminobiphenylHMDB
p,P'-dianilineHMDB
p,p-BianilineHMDB
Rcra waste number u021HMDB
[1,1'-Biphenyl]-4,4'-diamineHMDB
[1,1'-Biphenyl]-4,4'-diamine (acd/name 4.0)HMDB
{[1,} 1'-biphenyl]-4,4'-diamineHMDB
Benzidine hydrochlorideHMDB
Benzidine acetateHMDB
Benzidine monosulfateHMDB
Benzidine dihydrochlorideHMDB
Chemical FormulaC12H12N2
Average Molecular Weight184.2371
Monoisotopic Molecular Weight184.100048394
IUPAC Name4-(4-aminophenyl)aniline
Traditional Namebenzidine
CAS Registry Number92-87-5
SMILES
NC1=CC=C(C=C1)C1=CC=C(N)C=C1
InChI Identifier
InChI=1S/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2
InChI KeyHFACYLZERDEVSX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzidines. These are organic compounds containing the benzidine skeleton, made up of a biphenyl ring system substituted at the 4- and 4'-positions with a unsubstituted amine group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBenzidines
Alternative Parents
Substituents
  • Benzidine
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point120 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.32 mg/mL at 25 °CNot Available
LogP1.34Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP10(1.59) g/LALOGPS
logP10(1.96) g/LChemAxon
logS10(-2.7) g/LALOGPS
pKa (Strongest Basic)4.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.6 m³·mol⁻¹ChemAxon
Polarizability21.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.00531661259
DarkChem[M-H]-142.69831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzidineNC1=CC=C(C=C1)C1=CC=C(N)C=C13170.0Standard polar33892256
BenzidineNC1=CC=C(C=C1)C1=CC=C(N)C=C11992.8Standard non polar33892256
BenzidineNC1=CC=C(C=C1)C1=CC=C(N)C=C12126.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzidine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(C2=CC=C(N)C=C2)C=C12333.3Semi standard non polar33892256
Benzidine,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(C2=CC=C(N)C=C2)C=C12403.4Standard non polar33892256
Benzidine,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(C2=CC=C(N[Si](C)(C)C)C=C2)C=C12543.8Semi standard non polar33892256
Benzidine,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(C2=CC=C(N[Si](C)(C)C)C=C2)C=C12652.7Standard non polar33892256
Benzidine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C2419.0Semi standard non polar33892256
Benzidine,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C2378.0Standard non polar33892256
Benzidine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C12510.8Semi standard non polar33892256
Benzidine,3TMS,isomer #1C[Si](C)(C)NC1=CC=C(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C12600.6Standard non polar33892256
Benzidine,4TMS,isomer #1C[Si](C)(C)N(C1=CC=C(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C2555.0Semi standard non polar33892256
Benzidine,4TMS,isomer #1C[Si](C)(C)N(C1=CC=C(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C=C1)[Si](C)(C)C2620.2Standard non polar33892256
Benzidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=C(N)C=C2)C=C12571.0Semi standard non polar33892256
Benzidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=C(N)C=C2)C=C12589.2Standard non polar33892256
Benzidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C13015.4Semi standard non polar33892256
Benzidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C=C13054.2Standard non polar33892256
Benzidine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C2871.2Semi standard non polar33892256
Benzidine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(C2=CC=C(N)C=C2)C=C1)[Si](C)(C)C(C)(C)C2819.8Standard non polar33892256
Benzidine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C13236.8Semi standard non polar33892256
Benzidine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C13258.7Standard non polar33892256
Benzidine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1)[Si](C)(C)C(C)(C)C3451.9Semi standard non polar33892256
Benzidine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C=C1)[Si](C)(C)C(C)(C)C3497.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzidine EI-B (Non-derivatized)splash10-001i-1900000000-46465bd7171400dfc5502017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzidine EI-B (Non-derivatized)splash10-001i-1900000000-46465bd7171400dfc5502018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1900000000-da909bc8739471b977a52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-0c34c7cea9097e35e7e12014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-000i-0900000000-36d2368b345aadafe4722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-014i-0900000000-c5c1dcbf033fe4c60c262017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-014i-0900000000-d5e0ce902c65a7d945a12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-014i-0900000000-527aa9bf80b6331854782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-014i-0900000000-d455d086a3a2f8252f642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-000i-0900000000-8a4d7fb696a251cf65f22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-000i-0900000000-9894faa005f0ae52dc532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-014r-0900000000-0b8ab8dbf459dd7787732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-014i-0900000000-497ea7121bf277833bb62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-014i-0900000000-6af8bfce4a24520cec002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-014i-0900000000-91749c0c5e4ef529093e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-014i-0900000000-49669661b9cd83218acb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-014i-0900000000-a61957b37aba01bd4ee02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine ESI-ITFT , positive-QTOFsplash10-00kr-1900000000-c4a27064ec37d84f03552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine APCI-ITFT , positive-QTOFsplash10-014i-0900000000-5f242ea7ebce9e040adf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine APCI-ITFT , positive-QTOFsplash10-014i-0900000000-6ee5a8d18cf5b5e520e32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine APCI-ITFT , positive-QTOFsplash10-014i-0900000000-bfa10df85ed8a268fafc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine APCI-ITFT , positive-QTOFsplash10-014i-0900000000-fccc4a1798517c633d702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzidine APCI-ITFT , positive-QTOFsplash10-014i-0900000000-df132eef993f855e82ed2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzidine 10V, Positive-QTOFsplash10-000i-0900000000-7e5627a8d5f62d9aa7e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzidine 20V, Positive-QTOFsplash10-000i-0900000000-39f67531ed6e9de51ade2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzidine 40V, Positive-QTOFsplash10-056r-1900000000-9a354370a58dd3accdf92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzidine 10V, Negative-QTOFsplash10-001i-0900000000-9d1762ff8a90d74258372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzidine 20V, Negative-QTOFsplash10-001i-0900000000-9d1762ff8a90d74258372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzidine 40V, Negative-QTOFsplash10-001i-2900000000-caeb9b49b279ff5b605f2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6844
KEGG Compound IDC16444
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzidine
METLIN IDNot Available
PubChem Compound7111
PDB IDNot Available
ChEBI ID80495
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Arlt M, Scheffler A, Suske I, Eschner M, Saragi TP, Salbeck J, Fuhrmann-Lieker T: Bipolar redox behaviour, field-effect mobility and transistor switching of the low-molecular azo glass AZOPD. Phys Chem Chem Phys. 2010 Nov 7;12(41):13828-34. doi: 10.1039/c0cp00643b. Epub 2010 Sep 20. [PubMed:20852800 ]
  2. Lardo MM, Diaz NB, Artaza JR, Carbia CD, Nazer R, Valdez R: [Vitamin E as protective agent against hemolysis in leprosy patients under dapsone treatment]. Medicina (B Aires). 1997;57(2):150-4. [PubMed:9532824 ]